US7598215B2 - Hydroxyl-containing surfactants with low surface tension and their use thereof - Google Patents

Hydroxyl-containing surfactants with low surface tension and their use thereof Download PDF

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US7598215B2
US7598215B2 US11/277,184 US27718406A US7598215B2 US 7598215 B2 US7598215 B2 US 7598215B2 US 27718406 A US27718406 A US 27718406A US 7598215 B2 US7598215 B2 US 7598215B2
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US20060217284A1 (en
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Petra Hinrichs
Kathrin Lehmann
Isabella Ulrich-Brehm
Bernd Weyershausen
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Evonik Operations GmbH
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Goldschmidt GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating compositions

Definitions

  • the invention relates to low surface tension surfactants containing hydroxyl groups, and to their use as surfactants in aqueous coating formulations.
  • Water-based paints and coatings are used on a large scale industrially.
  • Critical to effective wetting of the substrate is the lowering of the surface tension of the aqueous system by means of a surfactant.
  • a surfactant it is not only the lowering of the static surface tension to a small value that is decisive, but also the corresponding lowering of the dynamic surface tension.
  • a low dynamic surface tension is needed in particular for high-speed applications, for example, when applying coatings by spraying, or in printing operations.
  • the surfactants used must not disrupt the formation of a uniform film, must not cause any turbidity, and should be low-foaming—that means they should not promote the build-up of significant amounts of foam.
  • Water-based paints and coatings include formulations which, while being aqueous systems, include fractions of organic solvents alongside the water, such as is mandatory as a result, for example, of the use of glycols as antifreeze agents or used in the form of humectants in aqueous pigment pastes, or else as film-forming assistants or lowering the minimum film formation temperature of numerous aqueous dispersions.
  • nonionic surfactants such as alkylaryl ethoxylates or alcohol ethoxylates or ethylene oxide (EO)-propylene oxide (PO) copolymers are certainly capable of reducing the static surface tension
  • EO ethylene oxide
  • PO ethylene oxide
  • the high molecular weight and resultant low molecular mobility of these classes of compounds mean that it is not possible to lower the dynamic surface tension to a value which is acceptable to the user.
  • anionic surfactants such as the sodium salts of monoalkyl or dialkyl sulfosuccinates, are able effectively to reduce the dynamic surface tension, but using them leads to severe build-up of foam in application, and the finished coating reacts sensitively to water.
  • surfactants of this kind have been able to establish themselves convincingly in numerous applications. Their properties are attributed primarily to the rigid acetylenic alkyl spacer, which, as a result of the restricted degrees of freedom, imposes a kind of preorientation of polar and non polar groups. Responsibility for these properties is additionally ascribed to the small distance between the polar groups and to the low molecular weight ( ⁇ 300 g/mol), which allows the surfactant molecules to be highly mobile.
  • a problem with compounds of this type is that, in applications, foam build-up reoccurs after a very short time. For the user, however, it is very important to prevent this new foam build-up for as long as possible.
  • the alternative would be to add defoamers, whose possible consequences include unwanted defects in the formation of the coating film, and problems with interlayer adhesion.
  • the ecotoxicological evaluation of products based on 2,4,6,8-tetramethyl-5-decynediol is not unproblematic, and in addition the products are labeled at least with “Xi” (irritant).
  • Xi irritant
  • the invention accordingly first provides hydroxyl-containing surfactants obtained by reacting one or more epoxides of formula (I)
  • the invention further provides hydroxyl-containing surfactants obtained by reacting one or more epoxides of formula (I) above with at least one, or two or more, amine(s) of formula (III)
  • the invention further provides ether alcohols of the general formulae (IV) and (V)
  • the invention further provides amino alcohols of the general formulae (VI) and (VII)
  • the invention further provides for the use of the amino alcohols and/or ether alcohols of the invention as additives in aqueous formulations for, in particular, surface coatings, paints, printing inks or varnishes.
  • the invention further provides aqueous formulations comprising at least one of the amino alcohols and/or ether alcohols of the invention, such wetting agents being used normally in amounts from about 0.05% to about 5% by weight, preferably from about 0.1% to about 3% by weight.
  • the alcohols, amines, amino alcohols, and glycidyl ethers/esters used in accordance with the invention are industrial products which can be employed in the form of their respective commercially customary specifications, although in specialty applications of the amino alcohols and/or ether alcohols of the invention higher levels of purity may be required.
  • Particularly preferred residues R 1 in the epoxide are linear or branched aliphatic, cycloaliphatic, aromatic or aromatic-aliphatic residues having 3 to 12 carbon atoms.
  • Glycidyl ethers used include but are not limited to 2,3-epoxypropyl phenyl ether, 2,3-epoxypropyl isobutyl ether, 2,3-epoxypropyl 2′-ethylhexyl ether, 2,3-epoxypropyl 4′-tert-butyl phenyl ether, and the glycidyl ethers of various branched, primary alcohols such as Isofol® 10, Isofol® 12, Isofol® 16 and Isofol® 20 (Guerbet Alcohols from Sasol).
  • Glycidyl esters used include but are not limited to glycidyl neodecanoate, glycidyl 2-ethylhexanoate, and the glycidyl esters of various other aliphatic branched or unbranched carboxylic acids, such as Isocarb® 10, Isocarb® 12, Isocarb® 16, and Isocarb® 20 (Sasol Guerbet Alcohols oxidized to carboxylic acids).
  • Alcohols used include but are not limited to 1,4-butanediol, 1,4-butynediol, 1,4-butynediol ethoxylates and propoxylates (1 to 5 EO and/or PO/OH), 2,4,6,8-tetramethyl-5-decynediol and its ethoxylation products, isononanol and its ethoxylation/propoxylation products, glycerol, 1,2,6-hexanetriol, and polyalkylene glycols, such as polyethylene glycol, polypropylene glycol, polybutylene glycol, and other polyalkylene glycols which may be homopolymers or copolymers with a blockwise or random construction whose alkylene groups optionally are branched or are aromatic residues and whose average molecular weight is up to 1500 g/mol, more preferably between 200 and 1000 g/mol.
  • polyalkylene glycols such as polyethylene glycol, polypropy
  • Amines used include but are not limited to 1,6-hexamethylediamine, 3,3,5-(3,5,5)-trimethyl-1,6-hexamethylenediamine, the homologous series of the polyalkylene polyamines such as, for example, diethylenetriamine, triethylenetetraamine, and dipropylenetriamine, etc, and various polyoxyalkyleneamines (e.g., available from BASF or as Jeffamines® from Huntsman) having 1 to 3 amino functions.
  • polyalkylene polyamines such as, for example, diethylenetriamine, triethylenetetraamine, and dipropylenetriamine, etc
  • various polyoxyalkyleneamines e.g., available from BASF or as Jeffamines® from Huntsman having 1 to 3 amino functions.
  • Amino alcohols used include but are not limited to 6-amino-1-hexanol, ethanolamine, diethanolamine, triethanolamine, methyldiethanolamine, ethyldiethanolamine, dimethylethanolamine, diethylethanolamine, diisopropanolamine, and 2-dibutylaminoethanol.
  • the ether alcohols and amino alcohols claimed are prepared using glycidyl compounds and alcohols or amines, respectively, either, preferably, in amounts which are approximately equivalent, based on epoxide groups and reactive hydroxy or amine hydrogen atoms, or with an excess of hydroxy or amine hydrogen atoms.
  • the basis for calculation that is used is that of the OH number, amine number, and epoxide value, which are figures familiar to the skilled worker.
  • FIG. 1 depicts a comparison of the dynamic surface tension of the surfactants of the invention against non-inventive surfactants.
  • Determining the dynamic surface tension of the formulated systems is essential to be able to estimate the rate at which a wetting agent molecule reaches a newly generated interface in order to be able to make an active contribution to destroying foam.
  • a defined amount of wetting agent is added to a defined amount of a test system and is incorporated using a toothed-wheel disk at 1 500 rpm for 1 minute. Subsequently air is introduced at 3 000 rpm for 1 minute, and foam produced. The resulting foam height is read off and viewed in comparison with the foam height reached in the absence of the wetting agent. Thereafter a measurement is made of the time taken for the foam to go down completely, something which generally does not happen at all in the absence of wetting agents.
  • Foam is built up in a defined amount of a test system using a perforated disk (see below) at 2 000 rpm for 1 minute. Then a defined amount of wetting agent is placed on the foam and the occurrence of spontaneous defoaming is assessed visually (bursting air bubbles, “prickling” on the surface) and graded as absent ( ⁇ ), present (+/ ⁇ ) or very characteristic (+).
  • Shearing with the perforated disk is then repeated at 2 000 rpm for one minute. This time a stopwatch is used to record the time which elapses before foam builds up again. If a wetting agent is able to prevent foam building up again, it is classified, with “>60 s”, as very active.
  • a defined amount of this sample is subsequently introduced into a measuring cylinder and the foam height is recorded by reporting ml of foam and is compared with a blank sample.
  • the perforated disk employed actually comprises three disks arranged one above the other on a spindle (disk thickness 3 mm, disk diameter 25 mm) and each having three holes (diameter: 5 mm). The distance between the individual disks is 9 mm and they rotate vertically by 120° on the securing spindle.
  • This apparatus allows optimum introduction of macrofoam and microfoam, such as occurs in painting application operations (such as rolling or spraying, for example) and production processes and can be prevented by suitable wetting agents.
  • the sample is again stirred with the perforated disk at 2000 rpm for 1 minute and again the resulting foam height of the sample is read off in a measuring cylinder.
  • the wetting agent is still available in the system and hence is also found to be stable to hydrolysis.
  • wetting agents of the invention are labeled S1 to S7.
  • Noninventive, comparative examples are the following wetting agents, which are supplied as commercial products for aqueous systems and can be characterized in accordance with the details below.
  • JonCryl® ECO 2189 (glycol-ether-free, film-forming polymer dispersion) 1) 44.1 g
  • JonCryl® ECO 2177 (glycol-ether-free, film-forming polymer dispersion) 1) 17.7 g
  • Table 1 shows that using the wetting agents claimed in accordance with the invention significantly reduces foam build-up as compared with the blank sample and with the comparative examples.
  • the surfactants claimed in accordance with the invention neither exhibit the unsatisfactory water solubility and resultant unsatisfactory reduction in surface tension of, for example, comparative example V1 (solid hydrophobic substance), and nor, unlike for example V4 to V6, are they limited in terms of dynamic surface tension, which particularly with 10 bubbles/sec is relevant for rapid application operations.
  • the compounds of the invention exhibit pronounced spontaneous defoaming. It is this property of the innovative surfactants which is of greatest interest for the coatings manufacturer. If particular products such as S4 to S7 are still selected, it is additionally possible to obtain surfactants which are also notable for particularly low residual foam values as well, and which even on further introduction of shearing are capable of long-lasting foam prevention. As a consequence it is not necessary to add additional wetting agent or defoamer to the automotive finish system, even after storage.
  • 0.5% surfactant is weighed out into 10 g of a water-dilutable, self-crosslinking alkyd resin containing urethane groups, Resydrol VAZ 5541 (Solutia), and the surfactant is incorporated by stirring with a Hausschild Speedmixer at 3600 rpm for one minute.
  • the coating material is drawn down onto aluminum at 50 ⁇ m using a box-type applicator, in order to assess the compatibility.
  • the compounds claimed in accordance with the invention can be utilized without reserve as wetting agents in aqueous paints, inks, and other coating materials, since they significantly lower the surface tension, it being possible for these aqueous paints and inks to include, if desired, fractions of organic solvents.
  • a particularly interesting feature is that even in rapid application operations they become apparent as effective wetting agents, on account of their dynamic surface tension profile, which is virtually independent of the frequency, i.e., of the multiplicity of newly created interfaces.
  • the hydroxyl-containing surfactants claimed in accordance with the invention therefore combine, in a hitherto unknown profile of properties, spontaneous-defoaming properties, which are used during coatings manufacture and application, with vigorous foam destruction (residual foam values zero or very low).
  • spontaneous-defoaming properties which are used during coatings manufacture and application, with vigorous foam destruction (residual foam values zero or very low).
  • the last-mentioned property is found even after storage of the coating material, which implies that the compounds claimed in accordance with the invention are not subject to hydrolytic attack—that is, they are surprisingly stable.
  • the compounds claimed in accordance with the invention do not realize foam destruction at the cost of disrupted surface image, and so even sensitive automotive finish surfaces can be applied without defect.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
US11/277,184 2005-03-24 2006-03-22 Hydroxyl-containing surfactants with low surface tension and their use thereof Expired - Fee Related US7598215B2 (en)

Applications Claiming Priority (2)

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EP05006515A EP1705172B1 (de) 2005-03-24 2005-03-24 Hydroxylgruppen enthaltende Tenside mit geringer Oberflächenspannung und deren Verwendung
EP05006515.0 2005-03-24

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US20060217284A1 US20060217284A1 (en) 2006-09-28
US7598215B2 true US7598215B2 (en) 2009-10-06

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EP (1) EP1705172B1 (de)
CA (1) CA2535392C (de)
DE (1) DE502005000314D1 (de)
DK (1) DK1705172T3 (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080188673A1 (en) * 2005-03-24 2008-08-07 Goldschmidt Gmbh Ether Alcohol-Based Surfactants Having a Reduced Surface Tension and Use Thereof
US20100184913A1 (en) * 2008-12-05 2010-07-22 Thomas Ebbrecht Process for modifying surfaces
US8946369B2 (en) 2012-02-20 2015-02-03 Evonik Degussa Gmbh Branched polysiloxanes and use of these
US9845391B2 (en) 2013-12-20 2017-12-19 Evonik Degussa Gmbh Surface treatment of particles and their use
US12091579B2 (en) 2018-12-20 2024-09-17 Evonik Operations Gmbh Universal slip and flow control additives with recoatable quality

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008001674A1 (de) * 2008-05-09 2009-11-12 Evonik Goldschmidt Gmbh Flüssige Leitfähigkeitsadditive für nichtwässrige Hydrauliköle
WO2019232180A1 (en) * 2018-05-30 2019-12-05 Battelle Memorial Institute Cationic surfactants comprising an ether link
EP3875553A1 (de) * 2020-03-03 2021-09-08 Hubergroup Deutschland GmbH Hartharzlösung und wasserbasierter überdrucklack, der eine aminverbindung mit hydroxylgruppen enthält

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2997447A (en) 1954-02-08 1961-08-22 Air Reduction Aqueous acetylenic glycol compositions
EP0897744B1 (de) 1993-11-29 2001-02-07 Air Products And Chemicals, Inc. Wässriges Beschichtungsmittel und Tinte enthaltend ethoxylierte acetylenische Glycole mit niedriger dynamischer Oberflächenspannung
US6495727B1 (en) * 1998-11-05 2002-12-17 The Procter & Gamble Company Process for preparing ether-capped poly(oxyalkylated) alcohol surfactants
US20040077904A1 (en) * 2002-08-29 2004-04-22 Kao Corporation Production process for glycidyl ether adduct and catalyst used for the process

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6656977B2 (en) * 2001-07-20 2003-12-02 Air Products And Chemical, Inc. Alkyl glycidyl ether-capped polyamine foam control agents
US6746623B2 (en) * 2002-02-01 2004-06-08 Air Products And Chemicals, Inc. Alkyl glycidyl ether-capped diamine foam controlling agent
EP1505146A1 (de) * 2003-08-05 2005-02-09 Air Products And Chemicals, Inc. Bearbeitung von Substraten mit dichten Flüssigkeiten enthaltend acetylenische Diole und/oder Alkohole

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2997447A (en) 1954-02-08 1961-08-22 Air Reduction Aqueous acetylenic glycol compositions
EP0897744B1 (de) 1993-11-29 2001-02-07 Air Products And Chemicals, Inc. Wässriges Beschichtungsmittel und Tinte enthaltend ethoxylierte acetylenische Glycole mit niedriger dynamischer Oberflächenspannung
US6495727B1 (en) * 1998-11-05 2002-12-17 The Procter & Gamble Company Process for preparing ether-capped poly(oxyalkylated) alcohol surfactants
US20040077904A1 (en) * 2002-08-29 2004-04-22 Kao Corporation Production process for glycidyl ether adduct and catalyst used for the process

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080188673A1 (en) * 2005-03-24 2008-08-07 Goldschmidt Gmbh Ether Alcohol-Based Surfactants Having a Reduced Surface Tension and Use Thereof
US20100184913A1 (en) * 2008-12-05 2010-07-22 Thomas Ebbrecht Process for modifying surfaces
US8268939B2 (en) 2008-12-05 2012-09-18 Evonik Goldschmidt Gmbh Process for modifying surfaces
US8946369B2 (en) 2012-02-20 2015-02-03 Evonik Degussa Gmbh Branched polysiloxanes and use of these
US9845391B2 (en) 2013-12-20 2017-12-19 Evonik Degussa Gmbh Surface treatment of particles and their use
US12091579B2 (en) 2018-12-20 2024-09-17 Evonik Operations Gmbh Universal slip and flow control additives with recoatable quality

Also Published As

Publication number Publication date
EP1705172A1 (de) 2006-09-27
CA2535392A1 (en) 2006-09-24
DE502005000314D1 (de) 2007-02-22
DK1705172T3 (da) 2007-03-19
EP1705172B1 (de) 2007-01-10
US20060217284A1 (en) 2006-09-28
CA2535392C (en) 2013-11-12

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